9 Unlikely Oscar Couples

Love is certainly a mystery, isn’t it? If you were to look back at your own exes, I’m sure you’d have at least one person who’d make you go, “What was that? What was I thinking?!” I know I do. But all we can hope for from past relationships is a catalog of fond memories, life lessons learned, and maybe even a lasting bond between you and _____.

I wonder if these nine couples have that feeling. Do you think they look back fondly at these crazy vintage hairstyles and surprising Oscar® companions? I’d like to think so. Some of them are so adorable! And some are….quite interesting. Let’s go back in time to nine of the unlikeliest Oscar couples.

1. Brad Pitt and Gwyneth Paltrow

Image courtesy of Kevin Mazur/WireImage

At the time, these two made perfect sense, didn’t they? Seeing them now however, reminds of how on Parks and Rec, Anne Perkins changed herself into a female version of Chris Traeger and he immediately got bored dating her because he was essentially dating himself. Remember the matching short blonde bobs? RIP Bryneth. (Don’t think they ever had a celeb couple name – but this fits, eh?)

2. Sarah Jessica Parker and Robert Downey Jr.

Image courtesy of Barry King/WireImage

OH MY GOSH, look at this two! This looks more like a prom picture than an Oscar photo, but I’m kind of obsessed with it. Before SATC, and before Iron Man, there was SJP + RDJ = 2Getha4Eva

3. Christian Slater and Winona Ryder

Image courtesy of Ron Galella/Getty Images

I suppose it isn’t unlikely that the most beautiful actress of the ’90s dated the dreamiest actor of the ’80s and ’90s, but it’s always fun to take a trip down celeb nostalgia lane, don’t you think? The two briefly dated in 1988 after filming Heathers together. And then came Johnny…

4. Julia Roberts and Kiefer Sutherland

Image courtesy of KMazur/WireImage

What the WHAT? I mean, I knew this happened, technically, but it’s still such a surprising pairing. What did they talk about? Was it a classic case of ‘bad boy chases after the good girl’? Oh, Jiefer, you still baffle me.

5. Ben Affleck and Jennifer Lopez

Image courtesy of Kevin Winter/Getty Images

I actually rooted for these two. She was Jenny from the Block after all! But alas, the NY girl and the Boston boy couldn’t make it work. Considering Ben’s love of the Red Sox, it definitely makes sense. #GoSox, and farewell, Bennifer.

6. Madonna and Michael Jackson

Image courtesy of Ron Galella/WireImage

Though their love only lasted one week, it began at the Oscars! A match made in pop star heaven, many wondered if it was a publicity stunt. WHO CARES? It was a magical celeb moment, now frozen in time. One that we can always look back on. Fake or real, this was a surprising, but spectacular Oscar pair!

7. January Jones and Josh Groban

Image courtesy of Jon Kopaloff/FilmMagic

Well hello, Ms. Jones! My, how Betty Draper has grown. Groban looks the same though. Still swoon-worthy with those curls. Did anyone else know this coupling occurred?

8. LeAnn Rimes and Andrew Keegan

Image courtesy of Evan Agostini / ImageDirect

You would think with the number of times I scribbled, “Mrs. Chrissa Keegan” on my diary that I would’ve kept myself apprised of every one of his lady-friends. This one slipped past me though. And I gotta say, even as a married adult woman, this one bothers me a little. Back off, LeAnn!

9. Cher and Val Kilmer

Image courtesy of Time & Life Pictures/Getty Images

Nothing Cher does really surprises me at this point. Same goes for Val Kilmer. They both have that ‘wild card’ vibe that’s so strong, it practically punches you in the face. They dated in the ’80s and she was 14 years older than him! We’ve been making Demi/Ashton jokes for how long? And Cher was the original celeb cougar. Way to go, girl.

Can’t wait to see how many new Oscar couples show up this year! Make sure you join our Oscar Night Twitter Party, Co-hosted by the lovely Shay Mitchell (@shaymitch)! Red Carpet coverage starts at 7pm EST / 4pm PST and we’ll be tweeting about the dresses, the speeches and all the other fun moments in between.

Also, submit your Instagram videos for a chance to win a new Sprint smartphone and an honorary place in Shay’s Framily for the night. Shay will also tweet at the winners!

1. Best Red Carpet Pose

2. Best Fake Cry

3. Best Surprise Face

4. Best Framily Photo

Follow these hashtags to join the conversation: #Framily, #HGparty, and #Oscars!

Oscar®, Oscars® and Academy Awards® are a registered trademarks of the Academy of Motion Picture Arts and Sciences.

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HelloGiggles is a positive online community for women (although men are always welcome!) covering the latest in beauty, fashion, lifestyle, female empowerment, culture, relationships, friendship, careers, and issues that matter most to young women’s lives. A platform for writers and artists to create and share, HelloGiggles welcomes reader contributions and publishes them daily. And now, we are growing beyond just the website to include video, film, television and events. We were founded by Zooey Deschanel, Molly McAleer, and Sophia Rossi in 2011 as a place on the Internet to inspire a smile. We’re still trying to do just that.